Hydrochloric Acid → tert-Butyl 3-(hydroxymethyl)azetidine-1-carboxylate

Participants

Reaction Steps

To a solution of 1-(tert-butoxycarbonyl)azetidine-3-carboxylic acid (2.0 g) in THF (30 ml) was added borane-dimethyl sulfide complex (4.0 ml; 10.0 M as borane) under ice-cooled bath, and the mixture was stirred for 8 hours at room temperature. 1 N HCl (10 ml) was added dropwise to the mixture under ice-cooled bath, and THF was removed under reduced pressure. The whole residue was extracted with EtOAc, and the extract was washed with brine and dried over MgSO4. Concentration under reduced pressure gave tert-butyl 3-(hydroxymethyl)azetidine-1-carboxylate (1.6 g).

Provenance & Evidence